This invention relates generally to adamantane derivatives and more specifically to substituted .alpha.-[2'-tricyclo[3.3.1.1..sup.3,7 ]decylidene]benzeneacetonitrile derivatives.
The compounds of this invention possess useful antihypoxia activity, that is they protect warm-blooded animals from the effects of oxygen deprivation. In addition, the title compounds exerted anti-inflammatory activity when tested in the carrageenin-induced rat paw edema assay.
The ethyl 2-adamantylidenecyanoacetate (1) has been used as a precursor in the synthesis of a series of antiviral adamantane-spiro-3'-pyrrolidones (2), and .alpha.-amino-1(or 2)-adamantylacetic acids [Lundahl et al., J. Med. Chem. 15, 129 (1972) and Gaspert et al., Croat, Chim. Acta 48, 169 (1976), respectively]. The latter compounds are important in view of the fact that some synthetic penicillin analogs, with excellent antibacterial activity and resistance to penicillinase, contain an .alpha.-amino-1-adamantylmethyl side chain [Godtfredsen, Brit. Pat. No. 1,074,331 (1967)]. The conversion of 2-adamantylidenecyanoethylacetate (1) into the corresponding 2-(dicyanomethylene)adamantane (3) has also been described [Van Hes et al., J. Med. Chem. 15, 132 (1972)]. ##STR2##